Dimethyl acetylenedicarboxylate → HCID 12918161, compound

HRID 1448677Notes

Reaction equation

HRID 1448677 reaction equation
[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3]([O:5][CH3:6])=[O:4].[C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2OC(=O)[S:21][N:20]=2)=[CH:15][CH:14]=1)#[N:12]>ClC1C=CC=CC=1Cl>[C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:2]([C:3]([O:5][CH3:6])=[O:4])=[C:1]([C:7]([O:9][CH3:10])=[O:8])[S:21][N:20]=2)=[CH:15][CH:14]=1)#[N:12]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 12437406HCID 12437406, compound

Product 1

HCID 12918161HCID 12918161, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

Dimethyl acetylenedicarboxylate (42.63 g, 0.4 mol) and 5-(p-cyanophenyl)-1,3,4-oxathiazol-2-one (20.42 g, 0.1 mol) were heated at reflux in o-dichlorobenzene for 10 hours. Volatile materials were removed under reduced pressure (1 mm). The red-brown residue contained at least three contaminants (g.c.) which were removed by crystallization from methanol. Four recrystallizations resulted in 18.1 g (0.0598 mol, 59.8%) of light yellow solid, m.p. 134°-135°.

Workup

  1. customVolatile materials were removed under reduced pressure (1 mm)
  2. customwere removed by crystallization from methanol
  3. customFour recrystallizations
  4. customresulted in 18.1 g (0.0598 mol, 59.8%) of light yellow solid, m.p. 134°-135°

Sources & evidence

ORD record
ord-27c50aee714f4691904f0c50d40970c4
Source dataset
uspto-grants-1980_02
Patent number
US04187099

Reaction notes

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